Like the other reply, being fit is most important, clothes will hang better. Buy used/vintage designer clothes. Stick to neutrals: blues, khakis, grays, black and white and the one or two colors that looks good on you (red or whatever). Accessories are where you express yourself, so keep the funky trendy patterns to ties, socks, handkerchiefs (if wearing a suit) or even hats. Find a good tailor and have him take in/let out your clothes to provide an even more structured fit for your body shape (for example, some men have longer legs or wider shoulders/hips). Most celebrities have even their basic t-shirts tailored. Staying fit, keeping the neutral colors and buying well-made clothes will extend the life of your wardrobe immensely as well as your save money. Also, learn how to properly care for your clothing. My man does this, and he's had the same clothes for going on 20 years now. He has a penchant for funky t-shirts and will throw a nice button-up over it if he's going casual. His biggest wardrobe investment is his work clothes (construction), he will have to buy new shorts every 2-3 years because those will get holes, covered in paint or the drawstring wears out.